Process of producing azo dyestuffs



Patented Mar. 3, 1931 UNITED STATES PATENT OFFICE KARL HEUSNER AND MAX SIMON, OF LEVERKUSENQNEAR COLOGNE-ON-THE-BHINE, GERMANY, ASSIGNORS TO GENERAL ANILINE WORKS, INC., 01 NEW YORK, N. Y.,

A CORPORATION OI DELAWARE PROCESS OI PRODUCING AZO DYESTUFFS No Drawing.

The present invention relates to the new compounds of the general formula:

SOaH

wherein R represents the residue of any diazo compound and R a benzene nucleus, which may be substituted.

These compounds are obtainable, for instance, by coupling any diazo compound with a sulfa-mimic acid of the benzene series such as the sulfaminic acid of aniline, a toluidine or a cresidine. They are, when dried and pulverized, generally reddish to brownish powders dying wool in yellow to orange shades. This reaction usually proceeds very uniformly producing the dyestuflt's with excellent yields and eliminating the formation of undesirable byor decomposition prod- 20. ucts, This is particularly valuable if it is desired to obtain the corresponding dyestuffs with the free amino group, as we have further found that the sulfo group of the sulfaminic acid can be easily eliminated, as for instance by boiling the sulfaminic azo compound in aqueous solution with dilute mineral. acids. By this procedure better yields and more uniform products are obtained than when coupling the free amino compound directly with therespectivediazo compound. a The dyestufls are generally reddish to brownish powders which dye wool in yellow to orwith an aqueous solution containing 28 parts soda ash and 23.9 parts of the sodium salt of Application filed March 26, 1926, Serial No. 97,759.

2-sulfamino-4-methyl-1-methoxy benzene of A the formula The dyestuif is isolated in the usual way; it

has most likely the formula wherein R represents the residue of any diazo compound, which dyestuffs are, when dried and pulverized, generally reddish to brownish powders dyeing wool in yellow to orange shades.

2. As a new product, the monoazo dyestuff having most probably the formula:

Q-CE mo.hN--ON=N being, when dried and pulverized, a brownish powder dyeing wool in yellow shades.

3. As new prducts,the compounds of the general formula:

WhereinR represents the'residueaofany diazo compound and R -a-benzene nucleus, which may be substituted. 4

In testimony whereof We-ha-ve.hereunto-set vi I KARLIiEUSNER. MAX SIMON. I 

